N-Chlorphthalimid

Bezeichnung:N-Chlorphthalimid

CAS-Nr3481-09-2

Englisch Name:N-Chlorophthalimide

CBNumberCB6265755

SummenformelC8H4ClNO2

Molgewicht181.58

MOL-Datei3481-09-2.mol

Synonyma

N-Chlorphthalimid

N-Chlorphthalimid physikalisch-chemischer Eigenschaften

Schmelzpunkt	188-198 °C (lit.)
Siedepunkt	315.1±25.0 °C(Predicted)
Dichte	1.56±0.1 g/cm3(Predicted)
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
Aggregatzustand	powder to crystal
pka	-3.53±0.20(Predicted)
Farbe	White to Almost white
InChI	InChI=1S/C8H4ClNO2/c9-10-7(11)5-3-1-2-4-6(5)8(10)12/h1-4H
InChIKey	WDRFYIPWHMGQPN-UHFFFAOYSA-N
SMILES	C1(=O)C2=C(C=CC=C2)C(=O)N1Cl
CAS Datenbank	3481-09-2(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36
RIDADR	1759
WGK Germany	1
HazardClass	8
PackingGroup	II
HS Code	29349990
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

N-Chlorophthalimide Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
White to pale yellow powder
Verwenden
N-Chlorophthalimide may be employed in the synthesis of:
- α-amino acetal
- α-amino nitro compounds
- vicinal diamine
- α,β-unsaturated vicinal haloamino nitro compound
It may also be used as a chlorination reagent for the synthesis of 3-(methylthio)oxindoles.
Allgemeine Beschreibung
N-Chlorophthalimide in anhydrous acetic acid serves as a useful oxidizing reagent for use in various direct titrimetric analyses. N-Chlorophthalimide can be synthesized by reacting phthalimide, t-butyl hypochlorite, water and t-butyl alcohol. It participates in the synthesis of 2-amino-3-benzoyl-α-(methylthio)phenylacetamide.
Synthese

136918-14-4

3481-09-2

General procedure for the synthesis of N-chlorophthalimide from 3-hydroxy-1H-isoindol-1-one: Anhydrous aluminum trichloride (AlCl3, 1 eq., 10 mmol, 1.36 g) was added to an anhydrous acetonitrile (CH3CN, 100 mL) solution of lead tetraacetate (Pb(OAc)4, 1 eq., 10 mmol, 4.52 g). The mixture was stirred at room temperature for 5 minutes before phthalimide (1 eq., 10 mmol, 1.5 g) was added. The resulting mixture was gently refluxed under nitrogen protection for 20 h and subsequently cooled to room temperature. The solvent was removed by rotary evaporation and the crude product was purified by column chromatography using pure dichloromethane (DCM) as eluent. Yield: 1.32 g, 71% yield.1H NMR (300 MHz, CDCl3): δ 7.94-7.91 (m, 2H), 7.82-7.79 (m, 2H) ppm.
Einzelnachweise
[1] Synthesis, 2009, # 16, p. 2797 - 2801
[2] Synlett, 2006, # 2, p. 194 - 200
[3] Catalysis Today, 2018, vol. 308, p. 94 - 101
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1302
[5] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 8, p. 163

N-Chlorophthalimide Upstream-Materialien And Downstream Produkte

N-Chlorphthalimid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

3481-09-2, N-Chlorophthalimide Verwandte Suche:

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